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L-Proline-catalysed synthesis of chromeno[2,3- b ]chromene from 4-hydroxy-2 H -chromene-2-thione and an anti-proliferative study.
- Source :
-
Organic & biomolecular chemistry [Org Biomol Chem] 2024 Jul 03; Vol. 22 (26), pp. 5333-5345. Date of Electronic Publication: 2024 Jul 03. - Publication Year :
- 2024
-
Abstract
- The reactivity of 4-hydroxy-2 H -chromene-2-thione is investigated with aryl aldehydes and 5,5-dimethylcylohexane-1,3-dione (dimedone) in the presence of 20 mol% L-proline in toluene at 90 °C. Instead of the expected linear product with a sulphur atom in the ring provided by 4-hydroxydithiocoumarin or an angular product obtained from 4-hydroxycoumarin, the hitherto unreported products, 12-aryl substituted chromeno[2,3- b ]chromenes (4), were obtained in good to excellent yields. The reaction proceeds through a three-component reaction via Knoevenagel condensation between dimedone with an aromatic aldehyde followed by Michael addition with 4-hydroxy-2 H -chromene-2-thione. In addition, a molecular docking study of all the derivatives was performed and among them, four compounds exhibited anti-proliferative activity and elevated ROS generation in breast cancer (MCF7) cell lines.
Details
- Language :
- English
- ISSN :
- 1477-0539
- Volume :
- 22
- Issue :
- 26
- Database :
- MEDLINE
- Journal :
- Organic & biomolecular chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 38853721
- Full Text :
- https://doi.org/10.1039/d4ob00509k